873-55-2|Sodium benzenesulfinate| Ambeed

CAS No. :	873-55-2
Formula :	C₆H₅NaO₂S
M.W :	164.16
SMILES Code :	O=S(C1=CC=CC=C1)[O-].[Na+]
MDL No. :	MFCD00013135
InChI Key :	CHLCPTJLUJHDBO-UHFFFAOYSA-M
Pubchem ID :	2723840

Safety of [ 873-55-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 873-55-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	33.76
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	59.34 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	-5.47
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.63
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.79
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.25
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.16
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.33

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.63
Solubility	3.82 mg/ml ; 0.0233 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.45
Solubility	5.81 mg/ml ; 0.0354 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.81
Solubility	2.52 mg/ml ; 0.0153 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.85 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.45

Application In Synthesis of [ 873-55-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 873-55-2 ]

[ 873-55-2 ] Synthesis Path-Downstream 1~33

1
[ 2895-21-8 ]
[ 873-55-2 ]
[ 71985-71-2 ]

References: [1]Canadian Journal of Chemistry,1979,vol. 57,p. 1958 - 1966.

2
[ 873-55-2 ]
[ 538-28-3 ]
[ 52427-29-9 ]

References: [1]Tetrahedron,1981,vol. 37,p. 37 - 44.

3
[ 873-55-2 ]
[ 459-57-4 ]
[ 66-39-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	In dimethyl sulfoxide; at 120℃; for 96h;	Sodium phenylsulfinate (16.4 g, 0.1 mol) and 4-fluorobenzaldehyde (12.4 g, 0.1 mol) were combined in dimethylsulfoxide (100 mL) and heated at 120C for 4 days. The cooled reaction was poured into water. The resulting crystals were filtered off and washed with water, then dissolved in ethyl acetate/dichloromethane, dried and concentrated in vacuo until crystallisation ensued. The mixture was diluted with isohexane and the crystals filtered off and washed with further isohexane to yield 4(phenylsulfonyl)benzaldehyde (19.6 g, 80%). δH (500 MHz, d6 DMSO): 10.06 (1 H, s), 8.16 (2 H, d, J = 8.3 Hz), 8.09 (2 H, d, J = 8.3 Hz), 7.99 (2 H, d, J = 7.7 Hz), 7.71 (1 H, t, J = 6.9 Hz), 7.63 (2 H, t, J = 7.7 Hz).
80%	In dimethyl sulfoxide; at 120℃; for 96h;	In the first step, 60 ml of DMSO was added to a 100 ml round bottom flask equipped with a condenser tube with stirring,Then, 8.2 g (0.05 mol) of sodium benzenesulfinate was added to the flask, 6.2 g (0.05 mol) of p-fluorobenzaldehyde,The reaction was then stirred at 120 4 days.After completion of the reaction, the mixture was cooled to room temperature,The reaction mixture was poured into a large amount of water,Precipitate the precipitate and wash it several times with water,The precipitate was then recrystallized three times with a mixed solvent of ethyl acetate / dichloromethane,To give 9.8 g of 4-benzenesulfonylbenzaldehyde in 80% yield;
41%	In dimethyl sulfoxide; at 100℃; for 20h;	A mixture of 4-fluorobenzaldehyde (6 g, 48 mmol), sodium benzenesulfinate (7.5 g, 4.6 mmol), and dimethylsulfoxide (30 ml_) was heated at 100 C for 20 hours. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated to give a white solid. A solution of this crude product and dichloromethane was evaporated over silica gel, and the resulting silica gel supported crude product was purified using flash chromatography (Analogix SuperFlash column, 15% - 40% ethyl acetate in hexanes) to give 4.29 g (41 %) of 4-(benzenesulfonyl)-benzaldehyde as a white solid.

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 4691 - 4692.
[2]Patent: WO2006/21805,2006,A1 .Location in patent: Page/Page column 58.
[3]Patent: CN106588935,2017,A .Location in patent: Paragraph 0039; 0040.
[4]Patent: WO2010/55005,2010,A1 .Location in patent: Page/Page column 90-91.
[5]Journal of Medicinal Chemistry,1996,vol. 39,p. 3984 - 3997.

4
[ 873-55-2 ]
[ 104-88-1 ]
[ 66-39-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	In dimethyl sulfoxide; at 180℃; for 1.5h;Microwave irradiation;	Example 35: (S)-4-(4-Benzenesulfonyl-benzyl)-2-phenyl-morpholine4-Benzenesulfonyl-benzaldehyde; A microwave vessel was charged with Ig of 4-chlorobenzaldehyde in 6mL of DMSO and 1.75g of sodium benzenesulfinate. The vessel was sealed and heated in a microwave reactor at 1800C for 1.5 hours. The mixture was cooled and poured into 12mL of ice water. Filtered and the solid was purified by flash chromatography using ethyl acetate/hexane as eluent mixtures to afford 1.34g of the title compound. 76 % yield.
76%	In dimethyl sulfoxide; at 180℃; for 1.5h;Microwave irradiation;	A microwave vessel was charged with Ig of 4-chlorobenzaldehyde in 6mL of DMSO and 1.75g of sodium benzenesulfmate. The vessel was sealed and heated in a microwave reactor at 180 oC for 1.5 hours. The mixture was cooled and poured into 12mL of ice water. Filtered and the solid was purified by flash chromatography using ethyl acetate/hexane as eluent mixtures to afford 1.34g of product. 76 % yield.
12%	With copper(l) iodide; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 150℃; for 1h;Microwave irradiation;	4-(phenylsulfonyl)benzaldehyde. The mixture of 4-chlorobenzaldehyde (1.4 g, 10 mmol) and sodium benzenesulfinate (1.7 g, 10 mmol) and CuT (190 mg, 1 mmol) and K2C03 (138 mg, 1 mmol) in NIVIP (10 mL) was stirred at 1 50C for 1 hr with the microwave. The mixture was quenched with H20 and extracted with EtOAc. The combined organic layer was washed with brine, dried over Mg504 and concentrated in vacuo. The residue was purified by columnchromatography (Petroleum ether:EtOAc =10:1) to give 4-(phenylsulfonyl)benzaldehyde (300 mg, yield 12%).

References: [1]Synlett,2011,p. 2750 - 2756.
[2]Patent: WO2008/48914,2008,A1 .Location in patent: Page/Page column 22.
[3]Patent: WO2007/118041,2007,A1 .Location in patent: Page/Page column 12-13.
[4]Journal of Organic Chemistry,1989,vol. 54,p. 4691 - 4692.
[5]Patent: WO2016/19588,2016,A1 .Location in patent: Page/Page column 110.

5
[ 10226-29-6 ]
[ 873-55-2 ]
[ 67886-01-5 ]

References: [1]Journal of the American Chemical Society,1978,vol. 100,p. 4858 - 4865.

6
[ 17641-08-6 ]
[ 873-55-2 ]
2-benzenesulfonyl-<i>N</i>-(3-methoxy-phenyl)-acetamide [ No CAS ]

References: [1]Magnetic Resonance in Chemistry,2000,vol. 38,p. 384 - 385.

7
[ 67442-07-3 ]
[ 873-55-2 ]
[ 258874-02-1 ]

References: [1]Synthesis,2000,p. 375 - 382.

8
[ 600-05-5 ]
[ 873-55-2 ]
[ 711-29-5 ]

References: [1]Synthesis,2007,p. 1465 - 1470.

9
[ 873-55-2 ]
[ 145349-76-4 ]
ethyl(4-(phenylsulfonyl)phenyl)sulfane [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 3405 - 3408.

10
[ 31736-73-9 ]
[ 873-55-2 ]
C₁₅H₁₃O₃SBr [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 4396 - 4405.

11
[ 873-55-2 ]
[ 73101-74-3 ]
[ 27628-41-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 18-crown-6 ether;	To 9.1 g (0.043 mol) of <strong>[73101-74-3]2-bromomethyl-benzooxazole</strong> in CH3CN (300 mL) were added 7.39 g (0.045 mol, 1.05 eq) of benzenesulfinic acid sodium salt and 2.27 g (8.6 mmol, 0.2 eq) of 18-crown-6. Stirring was continued overnight, solvent evaporated and a column chromatography afforded 8. 1 g (70%) of 2-benzenesulfonylmethyl-benzooxazole as a white solid, MS: 274 (H+). (Y. Nagao, S. Yamada, E. Fujita, Tet. Lett., 1983,24, 2291)

References: [1]Patent: WO2005/92856,2005,A1 .Location in patent: Page/Page column 95.

12
[ 873-55-2 ]
[ 104146-17-0 ]
[ 1161865-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; at 100℃; for 0.5h;	A mixture of <strong>[104146-17-0]4-chlorothiazole-5-carbaldehyde</strong> (0.15 g), benzenesulfinic acid sodium salt (0.25 g) and dimethyl sulfoxide (7.0 mL) was stirred at 1000C for 30 minutes. The mixture was cooled to room temperature, poured onto ice/water (50 mL) and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford the title compound as a tan oil (0.23 g).1H NMR (CDCI3): delta 7.57-7.63 (m, 2H), 7.67-7.73 (m, 1H), 8.11-8.14 (m, 2H), 8.95 (d, J = 0.9 Hz, 1 H), 10.83 (d, J = 0.9 Hz, 1 H).
	In dimethyl sulfoxide; at 100℃; for 0.333333h;	4-benzenesulfonylthiazole-5-carbaldehydeA mixture of <strong>[104146-17-0]4-chlorothiazole-5-carbaldehyde</strong> (2.9 g) and benzenesulfinic acid sodium salt (4.9 g) in anhydrous dimethyl sulfoxide (50 ml_) was heated at 1000C for 20 minutes. The resulting solution was cooled then poured onto a mixture of ice and saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound (5.03 g) as a pale yellow solid.1H NMR (300 MHz, CDCI3): delta 7.56-7.65 (m, 2H); 7.66-7.74 (m, 1 H); 8.09- 8.15 (m, 2H); 8.94 (d, J = 0.9 Hz, 1 H); 10.83 (d, J = 0.9 Hz, 1 H).

References: [1]Patent: WO2009/77728,2009,A1 .Location in patent: Page/Page column 74.
[2]Patent: WO2010/142934,2010,A1 .Location in patent: Page/Page column 32.

13
[ 1194-02-1 ]
[ 873-55-2 ]
[ 94341-56-7 ]

References: [1]Patent: WO2012/31197,2012,A1 .

14
[ 873-55-2 ]
[ 94341-56-7 ]

References: [1]Patent: WO2012/31199,2012,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.
[3]Patent: WO2013/127268,2013,A1 .

15
[ 14135-38-7 ]
[ 873-55-2 ]
[ 1394124-47-0 ]

References: [1]Chinese Journal of Chemistry,2012,vol. 30,p. 1611 - 1616.

16
[ 873-55-2 ]
[ 53449-14-2 ]
[ 1621182-16-8 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 90℃; for 6h;	Example (1)6-Nitro-7-(phenylsulfonyl)quinazolin-4(3H)-one (1) 7-chloro-6-nitroquinazolin-4(3H)-one (2 g, 8.87 mmcl) and benzenesulfinic acid sodium salt (1 .455 g, 8.87 mmol) were suspended in DMF (30 mL) and heated to 90C for 6 h. The reaction mixture was diluted with H20 (30 mL) and the precipitate was collected by vacuum filtration. The resulting solid was dried in vacuo to obtain 6-nitro-7-(phenylsulfonyl)quinazolin-4(3H)-one. 1H-1iMR (500,23 Mhz, [D6]DMSO) L: 12.97 (bs,1H), 8.61 (s, 1H) 8.52 (s, 1H), 8.42 (s, 1H), 8.05 (d, J=7.66 Hz, 2H), 778 (t, J=7.41 Hz, 1H), 7.70 (t, J7.81 Hz, 2H); 13C-NMR (12578 Mhz, [D6JDMSO) I: 159.7, 151.7, 150.2,144.7, 140.0, 1383, 135.15, 132.1, 130.2, 128.6, 127.2, 124.8; HR-MS (ESI, 4500V) m/z calculated for C14H9N3NaO5S (M+Na). 354 0155, found: 354.0146

References: [1]Patent: WO2014/118197,2014,A1 .Location in patent: Page/Page column 18; 19.

17
[ 4248-19-5 ]
[ 89891-69-0 ]
[ 873-55-2 ]
[ 1621273-04-8 ]

Yield	Reaction Conditions	Operation in experiment
3.35 g	With formic acid; In tetrahydrofuran; water; at 20℃; for 144.0h;	Formic acid (3.9 mE, 104 mmol) is added to a solution of tert-butyl carbamate (1.90 g, 16.2 mmol), 2-bromo-4- cyanobenzaldehyde (3.41 g, 16.2 mmol) and sodium benzenesulfinate (2.67 g, 16.2 mmol) in a mixture of tetrahydroffiran (7.0 mE) and water (60 mE), and the mixture is stirred at room temperature for 6 days. Water (180 mE) is added, and the precipitate is filtered and washed with water. The precipitate is treated with tert-butyl methyl ether (30 mE), and the mixture is stirred for 30 mm. The precipitate is filtered, washed with tert-butyl methyl ether, and dried. Yield:3.35g. ESI mass spectrum: [(7913r)-M+H]=451, [(8113r)-M+ H]=453; Retention time HPEC: 0.66 mm (X012_S01).
3.35 g	With formic acid; In tetrahydrofuran; water; at 20℃; for 144.0h;	Step 1:tert-Butyl (2-Bromo-4-cyanophenyl)(phenylsulfonyl)methylcarbamateFormic acid (3.9 mL, 104 mmol) is added to a solution of tert-butyl carbamate (1.90 g, 16.2 mmol), <strong>[89891-69-0]2-bromo-4-cyanobenzaldehyde</strong> (3.41 g, 16.2 mmol) and sodium benzenesulfinate (2.67 g, 16.2 mmol) in a mixture of tetrahydrofuran (7.0 mL) and water (60 mL),and the mixture is stirred at room temperature for 6 days. Water (180 mL) is added, and the precipitate is filtered and washed with water. The precipitate is treated with tert-butyl methyl ether (30 mL), and the mixture is stirred for 30 mm. The precipitate is filtered, washed with tert-butyl methyl ether, and dried. Yield: 3.35 g. ESI mass spectrum: [(79Br)- M+H] = 451, [(81Br)-M+H] = 453; Retention time HPLC: 0.66 min(XO12SO1).
3.35 g	With formic acid; In tetrahydrofuran; water; at 20℃; for 144.0h;	Formic acid (3.9 mL, 104 mmol) is added to a solution of tert-butyl carbamate (1.90 g, 16.2 mmol), <strong>[89891-69-0]2-bromo-4-cyanobenzaldehyde</strong> (3.41 g, 16.2 mmol) and sodium benzenes-ulfinate (2.67 g, 16.2 mmol) in a mixture of tetrahydrofurane (7.0 mL) and water (60 mL). The mixture is stirred at room temperature for 6 days. Water (180 mL) is added and the precipitate is filtered and washed with water. The precipitate is treated with tert-butyl methyl ether (30 mL), and the mixture is stirred for 30 min. The precipitate is filtered, washed with tert-butyl methyl ether and dried. Yield: 3.35 g. ESI mass spectrum: [(79Br)-M+H]+=451, [(81Br)-M+H]+=453; Retention time HPLC: 0.66 min (method X012_S01).

95.2 g	With formic acid; In tetrahydrofuran; water; at 15 - 25℃; for 144.0h;	Formic acid (65.2 mL, 1.73 mol) is added to a mixture of tert-butyl carbamate (31.6 g, 270 mmol), <strong>[89891-69-0]3-bromo-4-formylbenzonitrile</strong> (56.7 g, 270 mmol), sodium benzenesulfinate (44.3 g, 270 mmol), tetrahydofuran (170 mL) and water (340 mL). The mixture is stirred at room temperature for 6 days, and the precipitate is filtered. The precipitate is digested in acetonitrile (300 mL), filtered and washed with cold acetonitrile. Yield: 95.2 g. ESI mass spectrum: [(79Br)-M+H]+ = 451, [(81Br)-M+H]+ = 453; Retention time HPLC: 0.66 min (X012_S01).
26.8 g	With formic acid; In tetrahydrofuran; water; at 20℃; for 144.0h;	3-Bromo-4-formyl-benzonitrile (20.5 g, 97.7 mmol), benzenesulfmic acid sodium salt (16.03 g, 97.6 mmol) and tert-butylcarbamate (11.4 g, 97.7 mmol) are suspended in water (312 mL) and THF (78 mL). Formic acid (28.8 g, 625 mmol) is added and the solution is stirred at room temperature for 6 days. Water (300 mL) is added and the precipitate is filtered off, washed with water and dried. The crude product is further purified by precipitation from tert-butylmethylether. Yield: 26.8 g; ESI mass spectrum: [M+Na]+ = 473 (bromine isotope pattern).

References: [1]Patent: US2014/221335,2014,A1 .Location in patent: Paragraph 0307; 0308.
[2]Patent: WO2014/122160,2014,A1 .Location in patent: Page/Page column 67.
[3]Patent: US2016/31830,2016,A1 .Location in patent: Paragraph 0282.
[4]Patent: WO2016/16364,2016,A1 .Location in patent: Page/Page column 92-93.
[5]Patent: WO2016/16368,2016,A1 .Location in patent: Page/Page column 47.

18
[ 873-55-2 ]
[ 555-16-8 ]
[ 66-39-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With {(Pd{Fe(η5-C5H5)(η5-C5H3C(CH3)=NC6H4CH3-4)}(μ-Cl))2}; potassium carbonate; In dimethyl sulfoxide; at 110℃; for 12h;Inert atmosphere;	General procedure: Under N2 atmosphere, a reaction vessel was charged with a mixture of sodium sulfinates 1 (0.6 mmol), nitroarenes 2 (0.3 mmol), palladacycle I (0.75 mol%) and K2CO3 (1.0 equiv) in DMSO (2 ml) at room temperature. After that, the mixture was heated to 110 C and incubated in an oil bath for 12 h under N2 atmosphere. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with brine three times. The combined organic solution was dried with Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by thin-layer chromatography on silica gel GF 254 (ethyl acetate/petroleum ether) to give the pure product.

References: [1]Tetrahedron,2014,vol. 70,p. 9107 - 9112.

19
[ 873-55-2 ]
[ 111-92-2 ]
[ 5339-59-3 ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 987 - 992.

20
[ 6563-13-9 ]
[ 873-55-2 ]
6-methoxy-2-(phenylsulfonyl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; tert.-butylhydroperoxide; iron(III) chloride hexahydrate; In water; acetonitrile; at 80℃; for 12h;Schlenk technique;	General procedure: A Schlenk tube (35 ml) equipped with a magnetic bar was loaded with the solution of quinoline N-oxide 1 (0.5 mmol), sodium sulfinate 2 (1.0 mmol) and FeCl36H2O (20 mol%) in a mixture of CH3CN and H2O (5.0 ml, ca. 9:1 by volume). Then, TBHP (70% in decane, 1.0 mmol) and pyridine (1.0 mmol) were added to the solution dropwise via a syringe and the reaction mixture was stirred at 80 C for 12 h. After the completion of the reaction (monitored by thin layer chromatography), the mixture was washed with brine (15 ml) and then was extracted with dichloromethane (15 ml 3). The organic phase was combined and then concentrated. The oily crude product was purified by column chromatography using silica gel (-200-300 mesh) as stationary phase and a mixture of petroleum and ethyl acetate as eluent to give the desired product in the noted yields.
70%	With fluorosulfonyl fluoride; triethylamine; In dimethyl sulfoxide; at 40℃; for 16h;	General procedure: To a 25 mL double-necked flask was added 0.3 mmol of quinoline N-oxide, 0.9 mmol of sodium sulfonate, 1.5 mmol of Et3N, 2.5 mL of DMSO, and bubble SO2F2 into the mixture using a balloon combined with syringe needle. The mixture stirred for 16 h at 40 C. The reaction mixture was diluted with 5 mL of water, and extracted with CH2Cl2 (3*20 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was further purified through flash column chromatography using the mixture of petroleum ether and ethyl acetate as eluent (PE : EA=10 : 1 - 4 : 1).
54%	With ferric nitrate; In dimethyl sulfoxide; at 120℃; for 0.333333h;Microwave irradiation;	General procedure: Quinoline N-oxides 1 (0.3 mmol), sodium arylsulfinates 2 (0.45 mmol) and Fe(NO3)3 (0.09 mmol) in DMSO (3.0 mL) were added to a microwave reaction tube (5.0 mL). The reaction mixture was heated at 120 C for 20 min under microwave irradiation. After reaction completion, the solvent was distilled under vacuum. Ethyl acetate (10 mL) was added to the residue, and washed with saturated sodium chloride solution (3 × 30 mL). The organic phase was dried over anhydrous NaSO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired products 3 using ethyl acetate/petroleum ether (1:10 to 1:5) as the eluent. All compounds were confirmedby IR, 1H NMR, 13C NMR and MS.

References: [1]Chemical Communications,2015,vol. 51,p. 12111 - 12114.
[2]Synthetic Communications,2018,vol. 48,p. 1909 - 1918.
[3]Chemical Communications,2019,vol. 55,p. 13852 - 13855.
[4]Tetrahedron Letters,2020,vol. 61.
[5]Journal of Chemical Research,2017,vol. 41,p. 705 - 708.

21
[ 13331-27-6 ]
[ 873-55-2 ]
[ 2113-58-8 ]

References: [1]RSC Advances,2014,vol. 4,p. 57923 - 57928.

22
[ 54221-96-4 ]
[ 4248-19-5 ]
[ 873-55-2 ]
tert-butyl [(6-methoxypyridin-2-yl)(phenylsulfonyl)methyl]carbamate [ No CAS ]

References: [1]Chemistry - A European Journal,2016,vol. 22,p. 7879 - 7884.

23
[ 98197-88-7 ]
[ 873-55-2 ]
(4-(phenylsulfonyl)pyridin-2-yl)methanol [ No CAS ]

References: [1]Chemical Communications,2016,vol. 52,p. 11535 - 11538.
[2]Journal of Biomolecular NMR,2018,vol. 70,p. 77 - 92.

24
[ 87199-17-5 ]
[ 873-55-2 ]
[ 66-39-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	With [2,2]bipyridinyl; copper(II) bis(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 120℃;Microwave irradiation;	General procedure: Aryl boronic acid (0.3 mmol), sodium salt of aryl sulfinic acid (1.5 equiv), 2,2’-bipyridyl (20 mol %) and Cu(OTf)2 were placed in a microwave vial containing 4 mL of dichloroethane. The reaction mixture was then irradiated in MW (power 600 W, 120 C) for 20 to 30 min. After completion, water was added to reaction mixture and extracted with dichloromethane (2 x 10 mL). The organic layer was then dried (Na2SO4), evaporated, and purified with column chromatography using 7- 10 % of EtOAc in Hexane as eluent.

References: [1]Synthetic Communications,2017,vol. 47,p. 319 - 323.

25
[ 873-55-2 ]
[ 15164-44-0 ]
[ 66-39-7 ]

References: [1]Organic Letters,2018,vol. 20,p. 760 - 763.

26
[ 4248-19-5 ]
[ 873-55-2 ]
[ 146137-78-2 ]
tert-butyl ((2-fluoro-5-(trifluoromethyl)phenyl)(phenylsulfonyl)methyl)carbamate [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 526 - 529.

27
[ 873-55-2 ]
[ 1122-91-4 ]
[ 66-39-7 ]

References: [1]Chemistry - A European Journal,2020,vol. 26,p. 3484 - 3488.
[2]European Journal of Organic Chemistry,2018,vol. 2018,p. 1208 - 1210.
[3]Chemical Science,2018,vol. 9,p. 3186 - 3191.
[4]Chemical Science,2021,vol. 12,p. 6323 - 6332.

28
[ 32340-38-8 ]
[ 873-55-2 ]
[ 41024-57-1 ]

References: [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1611 - 1616.

29
[ 1520-70-3 ]
[ 873-55-2 ]
[ 2225-19-6 ]

Yield	Reaction Conditions	Operation in experiment
45%	With dichloro bis(acetonitrile) palladium(II); silver(I) acetate; In 1,4-dioxane; dimethyl sulfoxide; at 120℃; for 24h;Inert atmosphere; Schlenk technique;	General procedure: Under the argon atmosphere, a Schlenk tube (15 mL) equipped with a magnetic bar was loaded with the sulfonamide 1 (0.5 mmol), sodium arylsulfinates 2 (0.6 mmol, 1.2 equiv.), Pd(MeCN)2Cl2 (6.5 mg, 5 molpercent) and AgOAc (166.9 mg, 1.0 mmol) in one portion. Then, the mixture of 1,4-dioxane/DMSO (3.5 mL in a 9:1 ratio) was added to obtain a clear solution and the reaction mixture was allowed to stir at 120 °C for 24 h. After cooling to room temperature, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated and the oily crude product was purified by column chromatography using silica gel (200-300 mesh) as stationary phase and a petroleum ether and ethyl acetate (3/1) as eluent to give the N-aryl sulfonamides 3 in noted yields.

References: [1]Synthetic Communications,2018,vol. 48,p. 1436 - 1442.

30
[ 939-57-1 ]
[ 873-55-2 ]
[ 56361-21-8 ]

References: [1]Catalysis Communications,2019,vol. 127,p. 69 - 74.

31
[ 939-57-1 ]
[ 873-55-2 ]
[ 56361-21-8 ]

References: [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5578 - 5585.

32
[ 35979-69-2 ]
[ 873-55-2 ]
[ 83872-56-4 ]

Yield	Reaction Conditions	Operation in experiment
74.88%	With tetrabutylammomium bromide; In tetrahydrofuran; water; at 55 - 60℃; for 12h;Inert atmosphere;	Under nitrogen protection, add 0.025mol <strong>[35979-69-2]4-bromo-2-methyl-2-butanol</strong>, 0.0325mol sodium benzenesulfinate, 0.0005mol n-tetrabutylammonium bromide and 11.78g water to a 500mL dry three-necked bottle, Stir to dissolve until the system becomes clear, add 50mL THF, stir and warm to 55-60 for 12h;After the reaction was completed, THF was recovered under reduced pressure, 50 mL of n-hexane was added, stirred and dispersed at room temperature for 30 minutes, and the filter cake was rinsed with an appropriate amount of n-hexane. The filtrate was recovered under reduced pressure to recover n-hexane to obtain 2-methyl-4- (phenylsulfonyl) -2 -Butanol 5.11g, GC content 83.57%, yield based on <strong>[35979-69-2]4-bromo-2-methyl-2-butanol</strong> 74.88%.

References: [1]Patent: CN110981765,2020,A .Location in patent: Paragraph 0071; 0076-0078; 0079; 0084-0086; 0087; 0092-0095.

33
[ 37688-96-3 ]
[ 873-55-2 ]
C₂₀H₃₃BrO₂S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2022.

Historical Records

Technical Information

• Reactions of Benzene and Substituted Benzenes

Related Functional Groups of
[ 873-55-2 ]

Aryls

A846536 [25932-11-0]

Sodium benzenesulfinate dihydrate

Similarity: 1.00

A288742 [824-79-3]

Sodium 4-methylbenzenesulfinate

Similarity: 0.87

A204921 [824-80-6]

Sodium 4-fluorobenzenesulfinate

Similarity: 0.85

A273602 [670-98-4]

Methyl benzenesulfinate

Similarity: 0.83

A752002 [657-84-1]

Sodium p-toluenesulfonate

Similarity: 0.80

Precautionary Statements-General
Code	Phrase
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P342	If experiencing respiratory symptoms:
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P370	In case of fire:
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P378
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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Code	Phrase
P401
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P411 + P235	Keep cool.
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P501	Dispose of contents/container to ...
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Code	Phrase
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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
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Code	Phrase
H300	Fatal if swallowed
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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